CA2575702A1 - Oxindole oxazolidinones as antibacterial agents - Google Patents

Oxindole oxazolidinones as antibacterial agents Download PDF

Info

Publication number: CA2575702A1
Authority: CA; Canada
Prior art keywords: oxo; dihydro; indol; oxazolidin; ylmethyl
Prior art date: 2004-08-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002575702A

Other languages

English (en)

French (fr)

Inventor

Gary Wayne Luehr

Rama Jain

Adam Robert Renslo

Vara Prasad Venkata Nagendra Josyula

Mikhail Fedorovich Gordeev

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co LLC

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2004-08-06

Filing date

2005-07-19

Publication date

2006-02-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=35079333&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2575702(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2005-07-19 Application filed by Individual filed Critical Individual

2006-02-16 Publication of CA2575702A1 publication Critical patent/CA2575702A1/en

Status Abandoned legal-status Critical Current

Links

239000003242 anti bacterial agent Substances 0.000 title abstract description 14
SWQXEEHFZPJRLQ-UHFFFAOYSA-N 1,3-dihydroindol-2-one;1,3-oxazolidin-2-one Chemical class O=C1NCCO1.C1=CC=C2NC(=O)CC2=C1 SWQXEEHFZPJRLQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 147
150000003839 salts Chemical class 0.000 claims abstract description 18
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 29
208000015181 infectious disease Diseases 0.000 claims description 21
239000008194 pharmaceutical composition Substances 0.000 claims description 14
241000894006 Bacteria Species 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
NBWHJIXSBDVUSW-AWEZNQCLSA-N n-[[(5s)-2-oxo-3-(2-oxo-1-propan-2-yl-3h-indol-5-yl)-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2N(C(C)C)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O NBWHJIXSBDVUSW-AWEZNQCLSA-N 0.000 claims description 5
241000588621 Moraxella Species 0.000 claims description 4
241000186367 Mycobacterium avium Species 0.000 claims description 4
241000295644 Staphylococcaceae Species 0.000 claims description 4
230000037396 body weight Effects 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
241000606125 Bacteroides Species 0.000 claims description 3
241001112696 Clostridia Species 0.000 claims description 3
241000194032 Enterococcus faecalis Species 0.000 claims description 3
241000606790 Haemophilus Species 0.000 claims description 3
241000606768 Haemophilus influenzae Species 0.000 claims description 3
241000191963 Staphylococcus epidermidis Species 0.000 claims description 3
241000193996 Streptococcus pyogenes Species 0.000 claims description 3
AOOOFGNHVWLGDH-AWEZNQCLSA-N n-[[(5s)-2-oxo-3-(2-oxo-1-propan-2-yl-3h-indol-5-yl)-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(N(C(C)C)C(=O)C2)C2=C1 AOOOFGNHVWLGDH-AWEZNQCLSA-N 0.000 claims description 3
SAYXFILVMKDTKX-AWEZNQCLSA-N n-[[(5s)-2-oxo-3-(2-oxo-1-propyl-3h-indol-5-yl)-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound C=1C=C2N(CCC)C(=O)CC2=CC=1N1C[C@H](CNC(=O)CC)OC1=O SAYXFILVMKDTKX-AWEZNQCLSA-N 0.000 claims description 3
CKCQTEXEZAGYST-MHTVFEQDSA-N n-[[(5s)-3-(1-butan-2-yl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2N(C(C)CC)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O CKCQTEXEZAGYST-MHTVFEQDSA-N 0.000 claims description 3
GAONGLBFSVSJTG-CVRLYYSRSA-N n-[[(5s)-3-(1-butan-2-yl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound C=1C=C2N(C(C)CC)C(=O)CC2=CC=1N1C[C@H](CNC(=O)CC)OC1=O GAONGLBFSVSJTG-CVRLYYSRSA-N 0.000 claims description 3
BONOJKNXLOQNPU-AWEZNQCLSA-N n-[[(5s)-3-(1-cyclopropyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N(C2CC2)C(=O)C2)C2=C1 BONOJKNXLOQNPU-AWEZNQCLSA-N 0.000 claims description 3
OFLZTUSTDIPPEO-AWEZNQCLSA-N n-[[(5s)-3-(1-cyclopropyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(N(C2CC2)C(=O)C2)C2=C1 OFLZTUSTDIPPEO-AWEZNQCLSA-N 0.000 claims description 3
KSBMMBVVMHVMQO-ZDUSSCGKSA-N n-[[(5s)-3-(1-cyclopropyl-7-fluoro-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC2=C1N(C1CC1)C(=O)C2 KSBMMBVVMHVMQO-ZDUSSCGKSA-N 0.000 claims description 3
XUGFLGRLYBAWGE-ZDUSSCGKSA-N n-[[(5s)-3-(1-ethyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2N(CC)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O XUGFLGRLYBAWGE-ZDUSSCGKSA-N 0.000 claims description 3
JMDVOUPDMVWDOC-ZDUSSCGKSA-N n-[[(5s)-3-(1-ethyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound C=1C=C2N(CC)C(=O)CC2=CC=1N1C[C@H](CNC(=O)CC)OC1=O JMDVOUPDMVWDOC-ZDUSSCGKSA-N 0.000 claims description 3
RVHNBTXLGSQGKO-LBPRGKRZSA-N n-[[(5s)-3-(1-ethyl-7-fluoro-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C(F)=C2N(CC)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O RVHNBTXLGSQGKO-LBPRGKRZSA-N 0.000 claims description 3
UIHWLMLSYCJUGS-LBPRGKRZSA-N n-[[(5s)-3-(1-ethyl-7-fluoro-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound C=1C(F)=C2N(CC)C(=O)CC2=CC=1N1C[C@H](CNC(=O)CC)OC1=O UIHWLMLSYCJUGS-LBPRGKRZSA-N 0.000 claims description 3
HJLUONGHJAQWBR-LBPRGKRZSA-N n-[[(5s)-3-(1-methyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2N(C)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O HJLUONGHJAQWBR-LBPRGKRZSA-N 0.000 claims description 3
ISULWAUVGBCCNE-LBPRGKRZSA-N n-[[(5s)-3-(1-methyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(N(C)C(=O)C2)C2=C1 ISULWAUVGBCCNE-LBPRGKRZSA-N 0.000 claims description 3
OFQKHIZPJQEYBI-ZDUSSCGKSA-N n-[[(5s)-3-(7-fluoro-2-oxo-1-propan-2-yl-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C(F)=C2N(C(C)C)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O OFQKHIZPJQEYBI-ZDUSSCGKSA-N 0.000 claims description 3
CGECVMMVIWBLKL-ZDUSSCGKSA-N n-[[(5s)-3-(7-fluoro-2-oxo-1-propyl-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C(F)=C2N(CCC)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O CGECVMMVIWBLKL-ZDUSSCGKSA-N 0.000 claims description 3
YPPAANIBQSWQPH-ZDUSSCGKSA-N n-[[(5s)-3-(7-fluoro-2-oxo-1-propyl-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound C=1C(F)=C2N(CCC)C(=O)CC2=CC=1N1C[C@H](CNC(=O)CC)OC1=O YPPAANIBQSWQPH-ZDUSSCGKSA-N 0.000 claims description 3
DDDYIWRFHRWLLM-SBNLOKMTSA-N n-[[(5s)-3-[1-(1-fluoropropan-2-yl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2N(C(CF)C)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O DDDYIWRFHRWLLM-SBNLOKMTSA-N 0.000 claims description 3
RGFGXEJKPVZVHW-ZDUSSCGKSA-N n-[[(5s)-3-[1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(N(CCF)C(=O)C2)C2=C1 RGFGXEJKPVZVHW-ZDUSSCGKSA-N 0.000 claims description 3
LVUAQMUJXVYVGB-HNNXBMFYSA-N n-[[(5s)-3-[1-(cyclopropylmethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N(CC2CC2)C(=O)C2)C2=C1 LVUAQMUJXVYVGB-HNNXBMFYSA-N 0.000 claims description 3
TZWGREJRJNMHKT-HNNXBMFYSA-N n-[[(5s)-3-[1-(cyclopropylmethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C1=CC=C(N(CC2CC2)C(=O)C2)C2=C1 TZWGREJRJNMHKT-HNNXBMFYSA-N 0.000 claims description 3
DTUMCNVEKHECSI-AWEZNQCLSA-N n-[[(5s)-3-[1-(cyclopropylmethyl)-7-fluoro-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC2=C1N(CC1CC1)C(=O)C2 DTUMCNVEKHECSI-AWEZNQCLSA-N 0.000 claims description 3
PAQSGYVLEQRTQR-LBPRGKRZSA-N n-[[(5s)-3-[7-fluoro-1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC2=C1N(CCF)C(=O)C2 PAQSGYVLEQRTQR-LBPRGKRZSA-N 0.000 claims description 3
HKCYCGDBLBFEAY-LBPRGKRZSA-N n-[[(5s)-3-[7-fluoro-1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C(C=C1F)=CC2=C1N(CCF)C(=O)C2 HKCYCGDBLBFEAY-LBPRGKRZSA-N 0.000 claims description 3
RJFAPIOUDOUGSI-UHFFFAOYSA-N n-[[3-(7-fluoro-1-methyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C(F)=C2N(C)C(=O)CC2=CC=1N1CC(CNC(C)=O)OC1=O RJFAPIOUDOUGSI-UHFFFAOYSA-N 0.000 claims description 3
241000606161 Chlamydia Species 0.000 claims description 2
208000008960 Diabetic foot Diseases 0.000 claims description 2
206010014666 Endocarditis bacterial Diseases 0.000 claims description 2
208000001860 Eye Infections Diseases 0.000 claims description 2
241000192125 Firmicutes Species 0.000 claims description 2
206010031252 Osteomyelitis Diseases 0.000 claims description 2
208000005141 Otitis Diseases 0.000 claims description 2
206010057190 Respiratory tract infections Diseases 0.000 claims description 2
208000009361 bacterial endocarditis Diseases 0.000 claims description 2
208000019258 ear infection Diseases 0.000 claims description 2
206010014665 endocarditis Diseases 0.000 claims description 2
208000011323 eye infectious disease Diseases 0.000 claims description 2
201000007119 infective endocarditis Diseases 0.000 claims description 2
GARXZCYDHTYWFE-AWEZNQCLSA-N n-[[(5s)-2-oxo-3-(2-oxo-1-propyl-3h-indol-5-yl)-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound C=1C=C2N(CCC)C(=O)CC2=CC=1N1C[C@H](CNC(C)=O)OC1=O GARXZCYDHTYWFE-AWEZNQCLSA-N 0.000 claims description 2
FONAOGBLFYZWIG-NSHDSACASA-N n-[[(5s)-3-(7-fluoro-1-methyl-2-oxo-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C(C=C1F)=CC2=C1N(C)C(=O)C2 FONAOGBLFYZWIG-NSHDSACASA-N 0.000 claims description 2
QFLYAMKNEJSAMA-ZDUSSCGKSA-N n-[[(5s)-3-(7-fluoro-2-oxo-1-propan-2-yl-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]propanamide Chemical compound O=C1O[C@@H](CNC(=O)CC)CN1C(C=C1F)=CC2=C1N(C(C)C)C(=O)C2 QFLYAMKNEJSAMA-ZDUSSCGKSA-N 0.000 claims description 2
JXAZLXMPEDUOAF-ZDUSSCGKSA-N n-[[(5s)-3-[1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N(CCF)C(=O)C2)C2=C1 JXAZLXMPEDUOAF-ZDUSSCGKSA-N 0.000 claims description 2
208000020029 respiratory tract infectious disease Diseases 0.000 claims description 2
201000008827 tuberculosis Diseases 0.000 claims description 2
241000588655 Moraxella catarrhalis Species 0.000 claims 1
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 abstract description 19
150000005623 oxindoles Chemical class 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 421
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 148
238000002360 preparation method Methods 0.000 description 140
238000004128 high performance liquid chromatography Methods 0.000 description 121
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 116
239000007787 solid Substances 0.000 description 98
239000012267 brine Substances 0.000 description 89
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 88
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
239000000203 mixture Substances 0.000 description 85
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 82
229910052938 sodium sulfate Inorganic materials 0.000 description 82
235000011152 sodium sulphate Nutrition 0.000 description 82
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
239000007832 Na2SO4 Substances 0.000 description 71
238000006243 chemical reaction Methods 0.000 description 68
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 58
-1 bicyclic oxazolidinone derivatives Chemical class 0.000 description 50
235000019439 ethyl acetate Nutrition 0.000 description 50
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
229940093499 ethyl acetate Drugs 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
101150041968 CDC13 gene Proteins 0.000 description 29
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NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
238000003818 flash chromatography Methods 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
238000005160 1H NMR spectroscopy Methods 0.000 description 19
MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 18
239000002244 precipitate Substances 0.000 description 18
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239000007921 spray Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
UJMYZAYRKMULLR-UQKRIMTDSA-N tert-butyl N-[[(5S)-3-(1-cyclopropyl-7-fluoro-2-oxo-3H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate carbonyl dichloride Chemical compound C(=O)(Cl)Cl.C(C)(C)(C)OC(NC[C@H]1CN(C(O1)=O)C=1C=C2CC(N(C2=C(C1)F)C1CC1)=O)=O UJMYZAYRKMULLR-UQKRIMTDSA-N 0.000 description 1
MIQYNNNPCYQXBA-UQKRIMTDSA-N tert-butyl N-[[(5S)-3-(1-ethyl-2-oxo-3H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate carbonyl dichloride Chemical compound C(=O)(Cl)Cl.C(C)(C)(C)OC(NC[C@H]1CN(C(O1)=O)C=1C=C2CC(N(C2=CC1)CC)=O)=O MIQYNNNPCYQXBA-UQKRIMTDSA-N 0.000 description 1
KEIIOKXOKJWFAI-ZOWNYOTGSA-N tert-butyl N-[[(5S)-3-(1-ethyl-7-fluoro-2-oxo-3H-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate carbonyl dichloride Chemical compound C(=O)(Cl)Cl.C(C)(C)(C)OC(NC[C@H]1CN(C(O1)=O)C=1C=C2CC(N(C2=C(C1)F)CC)=O)=O KEIIOKXOKJWFAI-ZOWNYOTGSA-N 0.000 description 1
QTQREADTLQREAU-GNFRJPFZSA-N tert-butyl N-[[(5S)-3-[1-(1-fluoropropan-2-yl)-2-oxo-3H-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate carbonyl dichloride Chemical compound C(=O)(Cl)Cl.C(C)(C)(C)OC(NC[C@H]1CN(C(O1)=O)C=1C=C2CC(N(C2=CC1)C(CF)C)=O)=O QTQREADTLQREAU-GNFRJPFZSA-N 0.000 description 1
GLEMVWYUGFPIBQ-OAHLLOKOSA-N tert-butyl n-[(2r)-2-hydroxy-3-[(2-oxo-1-propyl-3h-indol-5-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC=C2N(CCC)C(=O)CC2=C1 GLEMVWYUGFPIBQ-OAHLLOKOSA-N 0.000 description 1
ZUSGVQMXADEURZ-FQNRMIAFSA-N tert-butyl n-[(2r)-3-[(1-butan-2-yl-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC=C2N(C(C)CC)C(=O)CC2=C1 ZUSGVQMXADEURZ-FQNRMIAFSA-N 0.000 description 1
IDYSPYDTFMFCLR-OAHLLOKOSA-N tert-butyl n-[(2r)-3-[(1-cyclopropyl-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound O=C1CC2=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC=C2N1C1CC1 IDYSPYDTFMFCLR-OAHLLOKOSA-N 0.000 description 1
YGCLIPSOSCUQIT-CQSZACIVSA-N tert-butyl n-[(2r)-3-[(1-cyclopropyl-7-fluoro-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound C1=2C(F)=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC=2CC(=O)N1C1CC1 YGCLIPSOSCUQIT-CQSZACIVSA-N 0.000 description 1
XPEUOACVQIALPK-CQSZACIVSA-N tert-butyl n-[(2r)-3-[(1-ethyl-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC=C2N(CC)C(=O)CC2=C1 XPEUOACVQIALPK-CQSZACIVSA-N 0.000 description 1
UYYHOFDZSUEAFV-CYBMUJFWSA-N tert-butyl n-[(2r)-3-[(1-ethyl-7-fluoro-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC(F)=C2N(CC)C(=O)CC2=C1 UYYHOFDZSUEAFV-CYBMUJFWSA-N 0.000 description 1
XYDAOLLNADTMHY-GFCCVEGCSA-N tert-butyl n-[(2r)-3-[(7-fluoro-1-methyl-2-oxo-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC(F)=C2N(C)C(=O)CC2=C1 XYDAOLLNADTMHY-GFCCVEGCSA-N 0.000 description 1
RTWVPLOGDJELEF-CQSZACIVSA-N tert-butyl n-[(2r)-3-[(7-fluoro-2-oxo-1-propan-2-yl-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC(F)=C2N(C(C)C)C(=O)CC2=C1 RTWVPLOGDJELEF-CQSZACIVSA-N 0.000 description 1
HNRNBWFGROREEV-CQSZACIVSA-N tert-butyl n-[(2r)-3-[(7-fluoro-2-oxo-1-propyl-3h-indol-5-yl)amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC(F)=C2N(CCC)C(=O)CC2=C1 HNRNBWFGROREEV-CQSZACIVSA-N 0.000 description 1
HJBPAGYHERGBPK-WPZCJLIBSA-N tert-butyl n-[(2r)-3-[[1-(1-fluoropropan-2-yl)-2-oxo-3h-indol-5-yl]amino]-2-hydroxypropyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H](O)CNC1=CC=C2N(C(CF)C)C(=O)CC2=C1 HJBPAGYHERGBPK-WPZCJLIBSA-N 0.000 description 1
VBLBMUZMFMXIJD-OAHLLOKOSA-N tert-butyl n-[(2r)-3-[[1-(cyclopropylmethyl)-7-fluoro-2-oxo-3h-indol-5-yl]amino]-2-hydroxypropyl]carbamate Chemical compound C1=2C(F)=CC(NC[C@@H](O)CNC(=O)OC(C)(C)C)=CC=2CC(=O)N1CC1CC1 VBLBMUZMFMXIJD-OAHLLOKOSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
GZULWOQMZNMQGN-RSAXXLAASA-N tert-butyl n-[[(5s)-2-oxo-3-(2-oxo-1-propyl-3h-indol-5-yl)-1,3-oxazolidin-5-yl]methyl]carbamate;carbonyl dichloride Chemical compound ClC(Cl)=O.C=1C=C2N(CCC)C(=O)CC2=CC=1N1C[C@H](CNC(=O)OC(C)(C)C)OC1=O GZULWOQMZNMQGN-RSAXXLAASA-N 0.000 description 1
LPLUWIGBFLNFPX-AWEZNQCLSA-N tert-butyl n-[[(5s)-3-(7-fluoro-2-oxo-1-propan-2-yl-3h-indol-5-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound C=1C(F)=C2N(C(C)C)C(=O)CC2=CC=1N1C[C@H](CNC(=O)OC(C)(C)C)OC1=O LPLUWIGBFLNFPX-AWEZNQCLSA-N 0.000 description 1
ZUPPHOQHPOLCIQ-CVRLYYSRSA-N tert-butyl n-[[(5s)-3-[1-(1-fluoropropan-2-yl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound C=1C=C2N(C(CF)C)C(=O)CC2=CC=1N1C[C@H](CNC(=O)OC(C)(C)C)OC1=O ZUPPHOQHPOLCIQ-CVRLYYSRSA-N 0.000 description 1
RCBSOQUNIYTGJN-HNNXBMFYSA-N tert-butyl n-[[(5s)-3-[1-(cyclopropylmethyl)-7-fluoro-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CNC(=O)OC(C)(C)C)CN1C(C=C1F)=CC2=C1N(CC1CC1)C(=O)C2 RCBSOQUNIYTGJN-HNNXBMFYSA-N 0.000 description 1
ASWYDKGGNIWGIM-ZDUSSCGKSA-N tert-butyl n-[[(5s)-3-[7-fluoro-1-(2-fluoroethyl)-2-oxo-3h-indol-5-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]carbamate Chemical compound O=C1O[C@@H](CNC(=O)OC(C)(C)C)CN1C(C=C1F)=CC2=C1N(CCF)C(=O)C2 ASWYDKGGNIWGIM-ZDUSSCGKSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229960003732 tyramine Drugs 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002575702A 2004-08-06 2005-07-19 Oxindole oxazolidinones as antibacterial agents Abandoned CA2575702A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US59982204P	2004-08-06	2004-08-06
US60/599,822		2004-08-06
PCT/IB2005/002196 WO2006016220A1 (en)	2004-08-06	2005-07-19	Oxindole oxazolidinones as antibacterial agents

Publications (1)

Publication Number	Publication Date
CA2575702A1 true CA2575702A1 (en)	2006-02-16

Family

ID=35079333

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA002575702A Abandoned CA2575702A1 (en)	2004-08-06	2005-07-19	Oxindole oxazolidinones as antibacterial agents
CA002576041A Abandoned CA2576041A1 (en)	2004-08-06	2005-07-19	Oxazolidinones containing oxindoles as antibacterial agents

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA002576041A Abandoned CA2576041A1 (en)	2004-08-06	2005-07-19	Oxazolidinones containing oxindoles as antibacterial agents

Country Status (24)

Country	Link
US (2)	US20080262056A1 (es)
EP (2)	EP1781642A1 (es)
JP (2)	JP2008509125A (es)
CN (1)	CN101001853A (es)
AP (1)	AP2007003904A0 (es)
AR (1)	AR050101A1 (es)
AU (1)	AU2005270951A1 (es)
BR (2)	BRPI0514020A (es)
CA (2)	CA2575702A1 (es)
EA (1)	EA200700322A1 (es)
GT (1)	GT200500204A (es)
IL (1)	IL180957A0 (es)
MA (1)	MA28793B1 (es)
MX (2)	MX2007001568A (es)
NL (1)	NL1029686C2 (es)
NO (1)	NO20071230L (es)
PA (1)	PA8640901A1 (es)
PE (1)	PE20060351A1 (es)
SV (1)	SV2006002180A (es)
TN (1)	TNSN07043A1 (es)
TW (1)	TWI289448B (es)
UY (1)	UY29048A1 (es)
WO (2)	WO2006016220A1 (es)
ZA (1)	ZA200700476B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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AU2006231919A1 (en) *	2005-04-06	2006-10-12	Pharmacia & Upjohn Company Llc	7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents
CA2603943A1 (en) *	2005-04-06	2006-10-12	Pharmacia & Upjohn Company Llc	An oxindole oxazolidinone as antibacterial agent
CN103420995B (zh) *	2013-09-07	2015-07-01	吉首大学	噁唑烷酮-烷胺基-呋喃酮型化合物及其制法和用途
CN103483329B (zh) *	2013-09-07	2015-08-05	吉首大学	呋喃酮-芳基-噁唑烷酮型化合物及其制法和用途
CN111018840B (zh) *	2017-10-25	2022-09-09	西南大学	3-咪唑取代的靛红唑醇类化合物及其制备方法和医药应用

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DE68918792T2 (de) *	1988-09-15	1995-03-30	Upjohn Co	5-Indolinyl-5-beta-amidomethyloxazolidin-2-one, 3-(substituierte kondensierte)phenyl-5-beta amidomethyloxazolidin-2-one und 3-(Nitrogen-substituierte)phenyl-5-beta-amidomethyloxazolidin-2-one.
US5164510A (en) *	1988-09-15	1992-11-17	The Upjohn Company	5'Indolinyl-5β-amidomethyloxazolidin-2-ones
DE4425612A1 (de) *	1994-07-20	1996-04-04	Bayer Ag	6-gliedrige stickstoffhaltige Heteroaryl-oxazolidinone
CN1046520C (zh) *	1994-11-15	1999-11-17	法玛西雅厄普约翰美国公司	二环噁嗪及噻嗪噁唑烷酮抗菌剂
HRP960159A2 (en) *	1995-04-21	1997-08-31	Bayer Ag	Benzocyclopentane oxazolidinones containing heteroatoms
CA2228647A1 (en) *	1995-09-01	1997-03-13	Pharmacia & Upjohn Company	Phenyloxazolidinones having a c-c bond to 4-8 membered heterocyclic rings
DE19601265A1 (de) *	1996-01-16	1997-07-17	Bayer Ag	2-Oxo- und 2-Thio-1,2-dihydrochinolinyl-oxazolidinone
DE19601627A1 (de) *	1996-01-18	1997-07-24	Bayer Ag	Heteroatomhaltige Cyclopentanopyridyl-Oxazolidinone
GB9601666D0 (en) *	1996-01-27	1996-03-27	Zeneca Ltd	Chemical compounds
GB9702213D0 (en) *	1996-02-24	1997-03-26	Zeneca Ltd	Chemical compounds
GB9609919D0 (en) *	1996-05-11	1996-07-17	Zeneca Ltd	Chemical compounds
ES2186916T3 (es) *	1996-08-21	2003-05-16	Upjohn Co	Derivados de isoxazolina como agentes antimicrobianos.
GB9717804D0 (en) *	1997-08-22	1997-10-29	Zeneca Ltd	Chemical compounds
JP2002501059A (ja) *	1998-01-23	2002-01-15	ファルマシア・アンド・アップジョン・カンパニー	オキサゾリジノンの組合せライブラリー、組成物および調製方法
GB9812019D0 (en) *	1998-06-05	1998-07-29	Zeneca Ltd	Chemical compounds
CA2359711A1 (en) *	1999-02-01	2000-08-03	Pharmacia & Upjohn Company	Process to prepare cyclic-sulfur fluorine containing oxazolidinones
DK1181288T3 (da) *	1999-05-27	2003-11-17	Upjohn Co	Bicycliske oxazolidinoner som antibakterielle midler
AR038536A1 (es) *	2002-02-25	2005-01-19	Upjohn Co	N-aril-2-oxazolidinona-5- carboxamidas y sus derivados
US7012088B2 (en) *	2003-02-24	2006-03-14	Pharmacia & Upjohn Company	Indolone oxazolidinones and derivatives thereof
AU2006231919A1 (en) *	2005-04-06	2006-10-12	Pharmacia & Upjohn Company Llc	7-fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents

2005
- 2005-07-19 JP JP2007524412A patent/JP2008509125A/ja active Pending
- 2005-07-19 BR BRPI0514020-0A patent/BRPI0514020A/pt not_active IP Right Cessation
- 2005-07-19 BR BRPI0513083-2A patent/BRPI0513083A/pt not_active IP Right Cessation
- 2005-07-19 WO PCT/IB2005/002196 patent/WO2006016220A1/en not_active Ceased
- 2005-07-19 EP EP05761010A patent/EP1781642A1/en not_active Withdrawn
- 2005-07-19 WO PCT/IB2005/002197 patent/WO2006016221A1/en not_active Ceased
- 2005-07-19 AP AP2007003904A patent/AP2007003904A0/xx unknown
- 2005-07-19 MX MX2007001568A patent/MX2007001568A/es unknown
- 2005-07-19 EP EP05761024A patent/EP1781643A1/en not_active Withdrawn
- 2005-07-19 EA EA200700322A patent/EA200700322A1/ru unknown
- 2005-07-19 AU AU2005270951A patent/AU2005270951A1/en not_active Abandoned
- 2005-07-19 CA CA002575702A patent/CA2575702A1/en not_active Abandoned
- 2005-07-19 JP JP2007524413A patent/JP2008509126A/ja active Pending
- 2005-07-19 CA CA002576041A patent/CA2576041A1/en not_active Abandoned
- 2005-07-19 MX MX2007001526A patent/MX2007001526A/es not_active Application Discontinuation
- 2005-07-19 US US11/573,161 patent/US20080262056A1/en not_active Abandoned
- 2005-07-19 CN CNA2005800266998A patent/CN101001853A/zh active Pending
- 2005-07-27 GT GT200500204A patent/GT200500204A/es unknown
- 2005-07-28 US US11/191,752 patent/US20060030609A1/en not_active Abandoned
- 2005-07-29 SV SV2005002180A patent/SV2006002180A/es not_active Application Discontinuation
- 2005-08-02 PA PA20058640901A patent/PA8640901A1/es unknown
- 2005-08-03 TW TW094126352A patent/TWI289448B/zh not_active IP Right Cessation
- 2005-08-03 UY UY29048A patent/UY29048A1/es not_active Application Discontinuation
- 2005-08-03 PE PE2005000905A patent/PE20060351A1/es not_active Application Discontinuation
- 2005-08-04 AR ARP050103255A patent/AR050101A1/es unknown
- 2005-08-05 NL NL1029686A patent/NL1029686C2/nl not_active IP Right Cessation
2007
- 2007-01-16 ZA ZA200700476A patent/ZA200700476B/xx unknown
- 2007-01-25 IL IL180957A patent/IL180957A0/en unknown
- 2007-02-05 TN TNP2007000043A patent/TNSN07043A1/fr unknown
- 2007-02-06 MA MA29668A patent/MA28793B1/fr unknown
- 2007-03-06 NO NO20071230A patent/NO20071230L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
AR050101A1 (es)	2006-09-27
WO2006016220A1 (en)	2006-02-16
ZA200700476B (en)	2008-10-29
JP2008509126A (ja)	2008-03-27
WO2006016221A1 (en)	2006-02-16
EA200700322A1 (ru)	2007-08-31
JP2008509125A (ja)	2008-03-27
EP1781643A1 (en)	2007-05-09
US20080262056A1 (en)	2008-10-23
UY29048A1 (es)	2006-03-31
PA8640901A1 (es)	2007-01-17
TNSN07043A1 (fr)	2008-06-02
NL1029686A1 (nl)	2006-02-07
AU2005270951A1 (en)	2006-02-16
SV2006002180A (es)	2006-06-26
PE20060351A1 (es)	2006-05-03
BRPI0513083A (pt)	2008-04-22
CA2576041A1 (en)	2006-02-16
IL180957A0 (en)	2007-07-04
CN101001853A (zh)	2007-07-18
TWI289448B (en)	2007-11-11
MX2007001526A (es)	2007-03-27
EP1781642A1 (en)	2007-05-09
US20060030609A1 (en)	2006-02-09
AP2007003904A0 (en)	2007-02-28
NO20071230L (no)	2007-05-04
MA28793B1 (fr)	2007-08-01
TW200612924A (en)	2006-05-01
BRPI0514020A (pt)	2008-05-27
GT200500204A (es)	2006-03-02
MX2007001568A (es)	2007-04-16
NL1029686C2 (nl)	2006-07-18

Publication	Publication Date	Title
CA2575702A1 (en)	2006-02-16	Oxindole oxazolidinones as antibacterial agents
EP1899331B1 (en)	2009-11-25	Homomorpholine oxazolidinones as antibacterial agents
US7435751B2 (en)	2008-10-14	7-Fluoro-1,3-dihydro-indol-2-one oxazolidinones as antibacterial agents
US20060229348A1 (en)	2006-10-12	Oxindole oxazolidinone as antibacterial agent
CA2637158A1 (en)	2007-08-16	Oxazolidinones containing oxindoles as antibacterial agents
CA2637811A1 (en)	2007-08-09	Benzisoxazole oxazolidinones as antibacterial agents
KR20070030952A (ko)	2007-03-16	항바이러스제로서 옥신돌을 함유하는 옥사졸리딘온
HK1104294A (en)	2008-01-11	Oxazolidinones containing oxindoles as antibacterial agents
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